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How to File Taxes Like a Boss

November 23, 2018 | By Daniel Dewitt

They say there’s nothing constant in the world besides death and taxes, and we certainly like to put both off till the last minute. While that may be a valid way of dealing with your own mortality, there’s no reason taxes have to be anywhere near as painful as we make them for ourselves.

Half of the reason we dislike them is because they involve math, but the other half is because we put them off for weeks if not months and then let the anxiety around them build for that whole period. So, why not try a different approach this year? Here are just a couple of ways to start on your taxes early and make them as least painful as possible.

File Online

The most hassle-free way of filing your taxes is to do it online. There are numerous online services dedicated to walking you step by step through the process and breaking it up into manageable chunks. After all, one of the worst parts of doing your taxes is not knowing where to start on them, and these online services structure the otherwise overwhelming task before you.

Most taxes are ultimately pretty straightforward, but if you’re not sure where to start they can seem labyrinthine. Instead of being on your own in trying to figure out what papers and documents you’ll need before you get started, an online service will let you know which ones you need when, and which documents you can safely discard.

Our personal online filing service of choice is TurboTax for its variety of features, clean and minimalist interface, and the important fact that it comes with a free version that will cover 90% of the needs of most tax filers. If the free version doesn’t cover everything you need, though, the premium version is relatively inexpensive to upgrade to, and can help you figure out how to work through anything from installment loans to self-employment expenses.

File Through an Accountant

If your taxes are too complicated for an online service to help you sort through, then it’s time to pull out the big guns and hire an accountant. While an accountant will invariably cost more than an online filing service, there’s a variety of cases where your just going to need to bite the bullet an consult an expert, like small business filings, insurance complications, or the death of a family member.

If you’re hesitant to hire an accountant, think of it like this: we don’t try and set our own bones or do heart surgery on ourselves, so why do we insist on doing the equivalent with our taxes? If your taxes are complicated enough to need an accountant, then often that accountant will be able to pay for themselves in the returns and exemptions they’ll be able to tease out of the tangle of your taxes.